## ClCH2COOH, chlororacetic acid

 H4 / O3 \ C1 = O2 / Cl6 - C5 / \ H7 H8
Tell me about the atomic charges, dipole moment, bond lengths, angles, bond orders,
molecular orbital energies, or total energy.
Tell me about the best Lewis structure.

## Atomic Charges and Dipole Moment

C1 charge= 0.743
O2 charge=-0.519
O3 charge=-0.557
H4 charge= 0.426
C5 charge=-0.448
CL6 charge=-0.081
H7 charge= 0.222
H8 charge= 0.216
with a dipole moment of 1.44084 Debye

## Bond Lengths:

between C1 and O2: distance=1.222 ang___ between C1 and O3: distance=1.363 ang___
between C1 and C5: distance=1.520 ang___ between C1 and H8: distance=2.142 ang___
between O2 and O3: distance=2.277 ang___ between O3 and H4: distance=0.984 ang___
between O3 and C5: distance=2.405 ang___ between C5 and CL6: distance=1.820 ang___
between C5 and H7: distance=1.103 ang___ between C5 and H8: distance=1.098 ang___

## Bond Angles:

for O3-C1-O2: angle=123.3 deg___ for H4-O3-C1: angle=106.3 deg___
for C5-C1-O2: angle=123.6 deg___ for CL6-C5-C1: angle=112.5 deg___
for H7-C5-CL6: angle=106.9 deg___ for H8-C5-CL6: angle=108.0 deg___

## Bond Orders (Mulliken):

between C1 and O2: order=1.973___ between C1 and O3: order=1.155___
between C1 and C5: order=0.857___ between C1 and H8: order=-0.054___
between O2 and O3: order=-0.212___ between O3 and H4: order=0.833___
between O3 and C5: order=-0.096___ between C5 and CL6: order=0.887___
between C5 and H7: order=0.957___ between C5 and H8: order=0.971___

## Best Lewis Structure

The Lewis structure that is closest to your structure is determined. The hybridization of the atoms in this idealized Lewis structure is given in the table below. Please note that your structure can't be well described by a single Lewis structure, because of extensive delocalization.

### Hybridization in the Best Lewis Structure

1. A bonding orbital for C1-O2 with 1.9972 electrons
__has 35.56% C 1 character in a sp1.89 hybrid
__has 64.44% O 2 character in a sp1.67 hybrid

2. A bonding orbital for C1-O2 with 1.9906 electrons
__has 27.36% C 1 character in a p3 hybrid
__has 72.64% O 2 character in a p3 hybrid

3. A bonding orbital for C1-O3 with 1.9964 electrons
__has 32.85% C 1 character in a sp2.46 hybrid
__has 67.15% O 3 character in a sp2.25 hybrid

4. A bonding orbital for C1-C5 with 1.9886 electrons
__has 48.79% C 1 character in a sp1.78 hybrid
__has 51.21% C 5 character in a sp2.71 hybrid

5. A bonding orbital for O3-H4 with 1.9879 electrons
__has 75.37% O 3 character in a s0.85 p3 hybrid
__has 24.63% H 4 character in a s orbital

6. A bonding orbital for C5-Cl6 with 1.9877 electrons
__has 44.93% C 5 character in a s0.79 p3 hybrid
__has 55.07% Cl 6 character in a s0.49 p3 hybrid

7. A bonding orbital for C5-H7 with 1.9828 electrons
__has 61.59% C 5 character in a sp2.85 hybrid
__has 38.41% H 7 character in a s orbital

8. A bonding orbital for C5-H8 with 1.9897 electrons
__has 61.82% C 5 character in a sp2.76 hybrid
__has 38.18% H 8 character in a s orbital

18. A lone pair orbital for O2 with 1.9776 electrons
__made from a sp0.62 hybrid

19. A lone pair orbital for O2 with 1.8858 electrons
__made from a p3 hybrid

20. A lone pair orbital for O3 with 1.9801 electrons
__made from a sp1.11 hybrid

21. A lone pair orbital for O3 with 1.8732 electrons
__made from a p3 hybrid

22. A lone pair orbital for Cl6 with 1.9981 electrons
__made from a sp0.17 hybrid

23. A lone pair orbital for Cl6 with 1.9833 electrons
__made from a p-pi orbital ( 99.98% p)

24. A lone pair orbital for Cl6 with 1.9770 electrons
__made from a p3 hybrid

139. A antibonding orbital for C1-O2 with 0.1386 electrons
__has 72.64% C 1 character in a p3 hybrid
__has 27.36% O 2 character in a p3 hybrid

-With core pairs on: C 1 O 2 O 3 C 5 Cl 6 Cl 6 Cl 6 Cl 6 Cl 6 -

#### Donor Acceptor Interactions in the Best Lewis Structure

The localized orbitals in your best Lewis structure can interact strongly. A filled bonding or lone pair orbital can act as a donor and an empty or filled bonding, antibonding, or lone pair orbital can act as an acceptor. These interactions can strengthen and weaken bonds. For example, a lone pair donor->antibonding acceptor orbital interaction will weaken the bond associated with the antibonding orbital. Conversly, an interaction with a bonding pair as the acceptor will strengthen the bond. Strong electron delocalization in your best Lewis structure will also show up as donor-acceptor interactions.
Interactions greater than 20 kJ/mol for bonding and lone pair orbitals are listed below.

The interaction of bonding donor orbital, 5, for O3-H4 with the antibonding acceptor orbital, 141, for C1-C5 is 24.7 kJ/mol.

The interaction of bonding donor orbital, 8, for C5-H8 with the antibonding acceptor orbital, 140, for C1-O3 is 21.3 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O2 with the antibonding acceptor orbital, 140, for C1-O3 is 174. kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O2 with the antibonding acceptor orbital, 141, for C1-C5 is 106. kJ/mol.

The interaction of lone pair donor orbital, 20, for O3 with the antibonding acceptor orbital, 138, for C1-O2 is 43.0 kJ/mol.

The interaction of the second lone pair donor orbital, 21, for O3 with the second antibonding acceptor orbital, 139, for C1-O2 is 235. kJ/mol.

The interaction of the third lone pair donor orbital, 24, for Cl6 with the antibonding acceptor orbital, 141, for C1-C5 is 28.6 kJ/mol.

## Molecular Orbital Energies

The orbital energies are given in eV, where 1 eV=96.49 kJ/mol. Orbitals with very low energy are core 1s orbitals. More antibonding orbitals than you might expect are sometimes listed, because d orbitals are always included for heavy atoms and p orbitals are included for H atoms. Up spins are shown with a ^ and down spins are shown as v.

28 ----- 1.870

27 ----- 0.411

26 ----- -0.522

25 ----- -2.483

24 -^-v- -7.011

23 -^-v- -7.535

22 -^-v- -7.939

21 -^-v- -8.484

20 -^-v- -10.24

19 -^-v- -10.49

18 -^-v- -11.20

17 -^-v- -12.15

16 -^-v- -12.29

15 -^-v- -12.84

14 -^-v- -15.75

13 -^-v- -18.33

12 -^-v- -21.72

11 -^-v- -25.85

10 -^-v- -28.14

9 -^-v- -190.3
8 -^-v- -190.3

7 -^-v- -190.8

6 -^-v- -248.8

5 -^-v- -268.7

4 -^-v- -270.6

3 -^-v- -506.9

2 -^-v- -508.3

1 -^-v- -2730.

## Total Electronic Energy

The total electronic energy is a very large number, so by convention the units are given in atomic units, that is Hartrees (H). One Hartree is 2625.5 kJ/mol. The energy reference is for totally dissociated atoms. In other words, the reference state is a gas consisting of nuclei and electrons all at infinite distance from each other. The electronic energy includes all electric interactions and the kinetic energy of the electrons. This energy does not include translation, rotation, or vibration of the the molecule.

Total electronic energy = -688.8116499297 Hartrees